Ahead of Obama center arrival, home sales are booming in small enclave of Jackson Park Highlands

Jackson Park Highlands residents Alisa Starks and Charlie Barlow discuss their landmark district neighborhood in South Shore and how it will be impacted by the nearby Obama Center. (Brian Cassella / Chicago Tribune)

Jackson Park Highlands residents Alisa Starks and Charlie Barlow discuss their landmark district neighborhood in South Shore and how it will be impacted by the nearby Obama Center. (Brian Cassella / Chicago Tribune)

If Jackson Park Highlands — the posh but tiny 16-square-block neighborhood of elegant, regal homes sitting at the foot of Jackson Park — is still a secret to most outside of the South Side, resident and businesswoman Alisa Starks said she doesn’t expect it to be for much longer.

The glare of the coming Obama Presidential Center and the proposed multimillion-dollar Tiger Woods golf course in Jackson Park have reflected brightly on nearby communities like hers, though she thinks the Highlands should be well-known for other reasons.

New homeowners receive more than just a literal welcome basket when they arrive in the tree-lined and neatly manicured Highlands. They’re introduced into an insular network where residents — professionals, academics and retirees — discuss neighborhood concerns, organize events like the annual Halloween party that draws hundreds of children, and alert neighbors when they’re leaving town on vacation.

“If someone’s gate’s open, we close it. If someone’s sick I make a pot of soup — it’s that type of neighborhood. That’s who we are,” said real estate agent Mary Ellen Holt, who moved to the Highlands in 2003 and has raised two daughters there. “With all of these amenities, when you add them all up there’s no place like this.”

More and more people have begun to discover the small enclave. Its proximity to the site of the Obama center plus a University of Chicago homeownership assistance program have boosted interest, and home sales are booming. Doctors, professors, lawyers and others say they have been attracted to the large homes that cost the same as two- or three-bedroom condos in other communities.

“I think it’s certainly kind of a hidden secret that this place is here,” said Charlie Barlow, the director of Roosevelt University’s Policy Research Collaborative, who moved into a three-story, 13-room American Foursquare-style home in the Highlands with his family and their boxer mix Baxter in July 2016. “(The Obama center) was announced after we moved in so it was very exciting for us to know that that was coming to the neighborhood.”

Brian Cassella / Chicago Tribune

Resident Charlie Barlow on his block March 6, 2018, in the Jackson Park Highlands neighborhood.

The Obama Foundation announced Jackson Park as the site of the presidential center in July 2016. The following year, Woodlawn, the closest neighborhood to the proposed site was declared a hot neighborhood by Redfin.com, a national real estate brokerage.

Now, Redfin.com says, the Highlands has joined Woodlawn as one of the hottest neighborhoods in Chicago — defined as an area with homes that are likely to be sold within two weeks. By that standard, the Highlands is comparable to the city’s other hot neighborhoods, including Bridgeport, Beverly, Hyde Park, and even the Gold Coast. But the number of Highlands homes available is far more limited than in other hot neighborhoods.

Since 2015, nearly 30 Highlands homes (11 percent) have been sold, according to property records.

Infused with new life and energy from new homeowners, some Highlands residents like Starks are hopeful that the presidential center could be the catalyst to revitalizing the struggling business corridor along East 71st Street, which could, in turn, help heal the troubled greater South Shore community, of which the Highlands is a part.

Historic homes

An anomaly among South Side neighborhoods, the Highlands is a diverse, active, upscale community with massive homes that are a throwback to the decades when South Shore was a getaway for the rich in the 1900s. A swampy farmland during the time of early settlers, the Highlands was built as an 80-acre subdivision starting in 1905 by attorney and Chicago Ald. Frank Ira Bennett, and was one of three planned communities within the expanding city. Because of its collection of homes designed by notable architects, the Highlands was designated a historic district in October 1989.

The Highlands’ homes are an inventive mix of architectural styles — from English Tudor and Greek Revival to French Provincial and Spanish Colonial — sitting on wide lots that would easily top $1 million in other neighborhoods. The area has also been home to a number of notable Chicagoans, including Nobel Prize-winning physicist Enrico Fermi, bluesman Bo Diddley, playwright David Mamet and the Rev. Jesse Jackson Sr., along with two of his sons.

In recent decades, the Highlands has lived in the shadow of South Shore, which has had its share of struggles since the steady erosion of the black middle-class base beginning in the 1990s. South Shore was also hit hard by the foreclosure crisis and has since been flooded with low-income renters with subsidy vouchers. These are two elements that residents have linked to street crime. And then there’s the loss of neighborhood staples like the Urban Partnership Bank, formerly ShoreBank, and the Dominick’s grocer at 71st Street and Jeffery Boulevard, that has yet to be replaced.

Russell Pike, president of the Jackson Park Highlands homeowner's association, one of the oldest in the city, would like to see a renewed business corridor along 71st Street between Yates Boulevard and Stony Island Avenue, but he remains skeptical that either the Obama center or the golf course would be the spark the area needs.

“I’m not sure if the golf course is going to create an avenue of businesses wanting to develop in that area. I’m not even sure if the Obama Center will do it as well, since (it’s) going to be” at least a mile north, he said. “What’s going to motivate someone to come another mile south?”

Pike also said he believes the spike in home sales lies not in the proximity to the presidential center, but to area beaches and lake trails, public transit and the area’s increased diversity.

"I wouldn't say that a lot of these changes has to do with the Obama Center. I don't know how far in advance people think 'Well I'm (going to) buy a house over here because in three years there's going to be the Obama center,’ " said Pike, 67. "I think the selling point is we're very community oriented (and) the neighbors look out for each other."

Even so,Highlands residents have found themselves increasingly on the front lines of heated discussions over the Obama center as fault lines between communities have emerged. The question is whether the center dedicated to the nation’s first black president will have a positive transformative effect on poorer communities. Some fear that the Obama center will cater to elite, highly educated blacks while working-class families will be left out.

Barlow, whose work with Roosevelt involves partnering with community groups to address social inequality, said he has felt some pushback from some of his new neighbors after he questioned the possible negative impact the Obama center could have on those most in need.

“I think we all have a responsibility — whether it’s local government, or elected officials, policymakers or the residents that live here — to hold ourselves to account and ensure that investments, whether it’s amenities, the proposed golf course, or the Obama Presidential Center, is beneficial to every resident that lives in South Shore,” Barlow said.

Development resurgence

Starks, a lifelong South Shore resident who moved into the Highlands as a new mom in 1997, is hoping to be part of the resurgence with plans to build an entertainment complex that includes a dine-in movie theater, restaurant and bowling alley on the site of the old ShoreBank branch on Jeffery Boulevard in May 2019.

Brian Cassella / Chicago Tribune

Resident Alisa Starks on her block March 6, 2018, in the Jackson Park Highlands neighborhood.

But the businesswoman, who was part of the team that founded the former ICE movie theaters in Chatham and Lawndale, said some of her hardest work has come after she was drafted to chair a special business development task force within the homeowner’s association. She and other Highlands residents are trying to learn what type of businesses and services their neighbors want while challenging them to get actively involved.

Highlands residents are insulated not only from the violence of the outer community, they’re also unaffected by the lack of options many other South Shore residents face, Starks said. Most if not all Highlands residents drive and can travel to Hyde Park and other places for grocery shopping and dine-in restaurant service, while poorer residents must rely on public transportation.

Starks blamed much of the disconnect between the Highlands and the outer community on a lack of communication, involvement and shared purpose between Highlands residents and community organizations.